Publication details
2,5-Dimethylphenacyl carbonates: A photoremovable protecting group for alcohols and phenols
| Authors | |
|---|---|
| Year of publication | 2005 |
| Type | Article in Periodical |
| Magazine / Source | Photochemical and Photobiological Sciences |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | photochemistry; phenacyl; protecting group |
| Description | Synthesis and photochemistry of a photochemically removable protecting group for alcohols and phenols, based on the 2,5-dimethylphenacyl (DMP) chromophore, is described. DMP carbonates release the corresponding hydroxy group containing molecules in high isolated yields (>70%), with quantum yields = 0.1-0.2 in methanol and = 0.36-0.51 in cyclohexane. The reactions proceed predominantly by the triplet pathway via E-photoenols, the lifetimes of which of approximately 2 s or 3 ms in cyclohexane or methanol, respectively, were determined by laser flash photolysis. |
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